


Pent Up

by DRHPaints



Category: Conan O’Brien, Late Night Host RPF, The Tonight Show with Conan O’Brien
Genre: Angry Sex, Blow Jobs, Conan O’Brien - Freeform, Dom/sub, Dominance, Established Relationship, F/M, Face-Fucking, Fingering, Orgasm Delay/Denial, Rough Sex, Submission, Taking Orders, angry Conan
Language: English
Status: Completed
Published: 2020-07-15
Updated: 2020-07-15
Packaged: 2021-03-05 05:40:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,397
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25289224
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Conan comes home after a particularly difficult day at the studio and surprises his girlfriend by showing her who’s boss.
Relationships: Conan O’Brien/Original Female Character
Kudos: 6





	Pent Up

**Author's Note:**

> If you enjoy this, please leave a comment or come say hi on Tumblr at fandomtransmandom :-)

Cassandra was standing over the stove stirring a beef stew. Conan was on his way from the studio and would be there soon and dinner was nearly ready, so she’d left the door unlocked. Hearing the handle open, she called over her shoulder, “Hey babe, how was your day?” and felt Conan walk up behind her.  
“Shut the fuck up,” he said, voice deadly flat.  
She began to turn, _“Excuse m—_ “ but before she could get out the second word a hand was placed over her mouth. He reached across her and turned off the stovetop burner.  
“I said shut. The fuck. Up,” Conan turned her fully to face him and she saw no light, no laughter behind his eyes as he stood before her in his suit. She breathed hard into his palm, unmoving. “You will do what I say when I tell you to say it. You move when I say move, you stop when I say stop. You say ‘yes, sir’ and ‘no, sir.’ Do you understand me?” He stared at her for a moment before slowly removing his palm from her mouth.  
Looking back at him with fire in her eyes, she paused for a moment before responding through her teeth. “Yes. Sir.”  
“Good,” he took a small step back from her. She’d never seen him look this angry. “Now take off your clothes.”  
“Yes, sir.” She said, quickly unbuttoning her dress.  
“No!” he practically shouted, startling her into freezing. “ _Slower_.” Cassandra began tantalizingly removing button by button, allowing the fabric of the dress to slither down her shoulders before delicately removing the loop of each bra strap and reaching back to remove it, holding it out to her side dramatically before dropping it to the ground. Slowly she hooked her thumbs underneath the waistband of her underwear and began inching them down her hips, eventually allowing them to pool at her feet before kicking them away from her. All the while she did not break eye contact with Conan, who was breathing hard through his nose and looking at her with a sharpness that was eerily foreign. Taking two fingers and pressing them firmly into the hollow of her throat, Conan turned her around, walking her backward until she was flush against the wall.   
“Put your arms over your head.”  
“Yes, sir,” she acquiesced. He pinned her hands together with his left fist, gripping hard, and leaned in to her, his face inches from hers. Trailing one finger down her midsection, his hand slid between her legs, separating her lips and beginning to stroke her, gently at first, then with an intensity that almost amounted to violence.   
When Cassandra’s eyes fell shut in ecstasy Conan slammed her hands against the wall and growled, “ _You keep your goddamn eyes on me._ ” She whipped them open and stared at him, at his chilly expression, and found it made her grind even harder into his hand. Moaning and struggling to keep her eyes open, Conan leaned even closer to her face, “Don’t you dare cum until I tell you to.” Cassandra tried to pull away, to lessen the friction, but there was no where to go but the wall and Conan persisted, twirling around her clitoris and pulsing against it harder and harder. She ground her teeth, clenched her toes, and dug her fingernails into her hands, anything to keep her threatening orgasm at bay. Soon she heard herself whining, she couldn’t help it, and still he did not relent.  
“ _Please, please..”_  
“Please, what?” He demanded.  
“ _Please, sir, let me cum, please,_ ” she heard herself begging, but she was beyond dignity, she was aching and her knees were buckling beneath her and she could taste blood from where she’d bit the inside of her cheek.  
Willing her eyes to stay open, they twitched helplessly, Conan leaned in and whispered in her ear, “ _Cum for me._ ” And it’s then that she let out an unearthly scream, cracking the back of her head against the wall as she pulsed up and down against his hand, shaking violently and being held up only by his left hand.  
Conan waited for her shaking to cease before letting go of her wrists and allowing her to sink to the floor. Cassandra knelt before him, looking up, breathing hard.  
“Unzip my pants,” Conan commanded. Cassandra obeyed, doing so slowly and intently.  
“Reach in and take out my cock.” She did and he was incredibly stiff, already dripping precum. She began to run her fingers up its length but almost immediately Conan swatted her hand away.  
“I didn’t say you could touch it, did I?”  
“No, sir,” Cassandra breathed, lowering her hand.   
He stared down at her. “Take the tip into your mouth. Don’t suck on it. Just hold it there.” Cassandra leaned forward to wrap her lips around him, tasting the salty-sweetness of it as she held it there, desperate to whip her tongue around and suck him deep into her throat, but holding still and peering into his flat eyes. Conan leaned forward and placed one hand behind her head, guiding her against the wall so that his hand was between her and the wall, and placed his other hand on the underside of her throat. “Now I’m going to fuck your face,” he murmured, tilting her head back and slowly sliding his cock into the back of her throat. “And you’re going to suck my cock. Do you understand?” She nodded as much as she was able in her restrained position and Conan began thrusting, delicately at first, but it wasn’t long before he was pummeling her face, saliva trailing from her mouth as he fucked the back of her throat, grunting and groaning as he rocked into her. “ _Don’t swallow it. Hold it in your mouth,”_ he panted in the seconds before he came. As he lost control, shooting into her mouth and holding her head tight, she fought the urge to swallow, doing her best not to choke. Conan withdrew and she looked at him, eyes watering. “Show me,” he said. She opened her mouth, displaying the cum, and Conan nodded. “You can swallow.” She did, gasping after and panting hard.  
Conan zipped up his pants and looked down at her, his expression softening. “You can stand up,” he said. Cassandra rose to her feet and Conan took her in his arms, nestling his head into her neck and holding her tight, rubbing her back slowly. “Was that okay?,” he whispered into her flesh.   
Reaching up to wrap her arms around him, she nodded. “Yeah.”  
“You’re okay?” he asked, soft, whispering.  
“Yeah. Yeah, I’m fine,” she said into his shoulder. After a beat. “Where’d that come from?”  
Conan pulled back, playing with her hair. “Well,” he began, looking at the floor, the ceiling. It seemed after all that intense eye contact he was having difficulty looking directly at her. “It was a particularly shitty day at work. I spent all day bowing and scraping for tv execs who were telling me how I was doing my job wrong, and on the way home all I could think was, “Goddamnit, I really wish there was some place where I was actually the boss.” And then it occurred to me that this might be worth trying…I hope it wasn’t too much.”  
“No,” Cassandra shook her head. “No, I really liked it. It caught me off-guard at first, but I liked it. To be honest I didn’t know you could get that…scary.”  
“Scary? Really?”  
“Yeah, I mean, your eyes, they were just…there was nothing there. I’ve never seen you look like that before. It was unnerving. But exciting, too,” Cassandra said, picking up her clothes from the floor.  
“I surprised myself a bit, too, if I’m honest,” Conan said, scratching the back of his neck. “I didn’t plan most of that. Didn’t know I had all that in me.”  
“See? That’s what gets buried when you’re nice to people all the time,” Cassandra said with a smile, pinching his arm as she pulled her clothes back on. “You bottle all that stuff up and you end up with a darkness you didn’t expect.”  
“Huh, I guess you’re right,” Conan said, half to himself. “Well, thanks for letting me explore it.” He leaned forward and kissed her.   
Cassandra nodded. “Anytime,” returning to the stove and reheating the stew.


End file.
